Dimitar Berbatov has revealed he would not be surprised if Harry Kane left Tottenham for a club like Manchester United, given he was in the exact same position.
Kane's future has been the source of constant speculation in recent weeks following reports he will look to leave Spurs unless they qualify for next season's Champions League.
The England captain, 27, so far has no silverware to show for his incredible career at Spurs, and his heroics have been in vain once again this season with the club languishing in seventh.
Although Berbatov won the League cup with Tottenham, something Kane has the chance to do next weekend against Manchester City, the Bulgarian found himself at a similar crossroads to the current Spurs star: stay and become a legend, or leave to win trophies?
Berbatov left for United, one of the clubs linked with Kane's signature, and never looked back, winning two Premier League titles and another League Cup.
Besides Teddy Sheringham, another man who made the same move, there is nobody better placed to wade in on Kane's dilemma, and Berbatov admits it's a tough decision.
He told Betfair : "It would be sad if he looks back in his career and has not been a Premier League champion at some point as he is one of the best strikers in the world.
"It's a tough decision as he is in a great environment, with a great stadium, training ground and more.
"The only thing missing for him is trophies."
And the former Spurs striker concedes he wouldn't be surprised if Kane finally left north London this summer.
He added: "I can see why Kane would want to move if they don't make the Champions League and if they don't win the League Cup.
"I would not be surprised as of course he wants to play Champions League football. It depends on how Spurs finish the season."
Kane is one of the top ten highest-scoring players in Premier League history and second on Tottenham's all-time list.
Another prolific season has him on track to overtake Jimmy Greaves as Tottenham's all-time top scorer, as well as Shearer's Premier League record - but he'll need to hang around in England's top-flight for a while longer.
Berbatov knows Kane will be worried about ruining his Tottenham legacy by joining a Premier League rival.
He continued: "I was Harry Kane at Tottenham once.
"I was in this position with the same decision and at the same club. There will be big thoughts going through his head.
"If he moves, he will be disappointing lots of Spurs fans. Some will turn against him, it is how it is in football.
"Fans take it personally and think that you are leaving, they feel that you've betrayed the club.
"My situation was similar, but also slightly different.
"I wanted to go to the biggest club to win trophies and that was Manchester United.
"When I heard there was a chance to go there, I did not hesitate."